(2R,3S,4R,5S,6R)-4-Acetoxy-6-[(S)-acetoxy-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-5-acetylamino-2-fluoro-3-phenylsulfanyl-tetrahydro-pyran-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (2R,3S,4R,5S,6R)-4-Acetoxy-6-[(S)-acetoxy-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-5-acetylamino-2-fluoro-3-phenylsulfanyl-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS No.: 146815-48-7
• Molecular Formula: C₂₅H₃₂FNO₁₀S
• Molecular Weight: 557.594
• Mol file: 146815-48-7.mol

Synonyms:(2R,3S,4R,5S,6R)-4-Acetoxy-6-[(S)-acetoxy-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-5-acetylamino-2-fluoro-3-phenylsulfanyl-tetrahydro-pyran-2-carboxylic acid methyl ester

Chemical Property of (2R,3S,4R,5S,6R)-4-Acetoxy-6-[(S)-acetoxy-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-5-acetylamino-2-fluoro-3-phenylsulfanyl-tetrahydro-pyran-2-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4R,5S,6R)-4-Acetoxy-6-[(S)-acetoxy-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-5-acetylamino-2-fluoro-3-phenylsulfanyl-tetrahydro-pyran-2-carboxylic acid methyl ester

There total 6 articles about (2R,3S,4R,5S,6R)-4-Acetoxy-6-[(S)-acetoxy-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-5-acetylamino-2-fluoro-3-phenylsulfanyl-tetrahydro-pyran-2-carboxylic acid methyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.0%

acetic anhydride (108-24-7) + (2R,3S,4R,5R,6R)-5-Acetylamino-6-[(S)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-2-fluoro-4-hydroxy-3-phenylsulfanyl-tetrahydro-pyran-2-carboxylic acid methyl ester (146788-04-7) → (2R,3S,4R,5S,6R)-4-Acetoxy-6-[(S)-acetoxy-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-5-acetylamino-2-fluoro-3-phenylsulfanyl-tetrahydro-pyran-2-carboxylic acid methyl ester (146815-48-7)

Guidance literature:

With pyridine; Ambient temperature;

DOI:10.1080/07328309608005696

Reference yield:

(2S,3S,4R,5S,6R)-4-Acetoxy-5-acetylamino-2-chloro-3-phenylsulfanyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester (120104-58-7) → (2R,3S,4R,5S,6R)-4-Acetoxy-6-[(S)-acetoxy-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-5-acetylamino-2-fluoro-3-phenylsulfanyl-tetrahydro-pyran-2-carboxylic acid methyl ester (146815-48-7)

Guidance literature:

Multi-step reaction with 5 steps

1: AgOTf, aq. Na₂HPO₄ / acetonitrile / 1.) r.t., 30 min, 2.) 50 deg C, 22 h

2: DAST / CH₂Cl₂ / 1 h / -78 °C

3: 91 percent / t-BuOK / methanol / 3 h / Ambient temperature

4: 76 percent / Dowex 50Wx₈ (H(+)-form) / 6 h / Ambient temperature

5: 85 percent / pyridine / Ambient temperature

With pyridine; disodium hydrogenphosphate; Dowex 50Wx₈ (H(+)-form); potassium tert-butylate; silver trifluoromethanesulfonate; 4,4'-diaminostilbene-2,2'-disulfonic acid; In methanol; dichloromethane; acetonitrile;

DOI:10.1080/07328309608005696

Reference yield:

(2R,3S,4R,5S,6R)-4-Acetoxy-5-acetylamino-2-fluoro-3-phenylsulfanyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester (146815-46-5) → (2R,3S,4R,5S,6R)-4-Acetoxy-6-[(S)-acetoxy-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-5-acetylamino-2-fluoro-3-phenylsulfanyl-tetrahydro-pyran-2-carboxylic acid methyl ester (146815-48-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / t-BuOK / methanol / 3 h / Ambient temperature

2: 76 percent / Dowex 50Wx₈ (H(+)-form) / 6 h / Ambient temperature

3: 85 percent / pyridine / Ambient temperature

With pyridine; Dowex 50Wx₈ (H(+)-form); potassium tert-butylate; In methanol;

DOI:10.1080/07328309608005696

upstream raw materials:

acetic anhydride

(2R,3S,4R,5R,6R)-5-Acetylamino-6-[(S)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-2-fluoro-4-hydroxy-3-phenylsulfanyl-tetrahydro-pyran-2-carboxylic acid methyl ester

(2S,3S,4R,5S,6R)-4-Acetoxy-5-acetylamino-2-chloro-3-phenylsulfanyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

(2R,3S,4R,5S,6R)-4-Acetoxy-5-acetylamino-2-fluoro-3-phenylsulfanyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

Downstream raw materials:

Methyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-5-deoxy-3-S-phenyl-3-thio-β-D-erythro-L-gluco-2-nonulopyranosylonate)-(2->8)-(5-acetamido-4,7,9-tri-O-acetyl-5-deoxy-3-S-phenyl-3-thio-β-D-erythro-L-gluco-2-nonulopyranosyl)onate fluoride

(2R,3S,4R,5S,6R)-4-Acetoxy-6-((1R,2R)-1-acetoxy-2,3-dihydroxy-propyl)-5-acetylamino-2-fluoro-3-phenylsulfanyl-tetrahydro-pyran-2-carboxylic acid methyl ester